Some thoughts on how to wear t-shirts

[Boss; Bosses; Moss]

The other week, my Twitter pal Tamsin asked if anyone had any advice for incorporating t-shirts into outfits in a more imaginative way then just the jeans-and-a… format.

Of course there’s nothing wrong with jeans-and-a-t-shirt; classic looks aren’t classic looks for nothing and really, who can be bothered to think about an outfit in any more detail most of the time? Also, if you have a badass t-shirt that’s an outfit right there – who cares about the rest?

Still, I aim to please and as a person with a pretty vast collection of shirts and zero pairs of jeans I reckon I’m moderately equipped to help out. So, here goes.

The bog-standard work outfit

[T-shirt; skirt; hat; earrings; bag; socks; shoes]

First things first. I don’t own any of the items in these outfit suggestions; except for this t-shirt and skirt. Just fantasising about how I’d wear them…

So for work, I like this skirt because it’s a classic shape but in a fairly unexpected finish. PVC in the office! You can only imagine the lols in the lifts. This skirt could be quite a sexy number, but as I don’t really do sexy and as this is for work purposes, I like to dress it down with this unsexy man’s t-shirt. The complementary colours mean it isn’t too weird and really, it’s not that much of a departure from wearing a white shirt with a black skirt.

I guess working in the ~~media allows me to wear things that are perhaps a bit more casual than standard office wear, but the gist of this is really t-shirt + skirt in complementary colour but interesting texture = one way to wear a cool t-shirt to the office.

For the sake of my fantastical shopping adventures, I went with accessories that are a bit bright and cheery while (hopefully) still maintaining a (slightly) grown-up feel. As for the hat, well. I just want to wear beanies every day at the moment and I do like them with earrings hanging out.

The night-out outfit

[T-shirt; skirt; jacket; bag; earrings; shoes]

I’m really into the idea of a cool monochrome graphic t-shirt and a bright skirt for a night out; feels nice and effortless but as though the right accessories would ensure you still felt a bit dressy. Again, I think adding a few smart elements in is key to making you look pulled together and as though you’ve made an effort – and not as though you’re some me, as a teenager, trying to try out something different.

I’m a huge fan of waist-length boxy jackets in the Chanel vein – they just make everything look a bit more pulled together and smart regardless of what’s going on underneath; the ideal pairing for a t-shirt.

This Rebecca Taylor boucle-and-leather combo is the dream for me right now – the perfect way of sneaking your way into looking like you’ve made an effort when really nothing could be further from the truth.

Ditto a nice handbag or shoes or jewellery – I know this is Cosmo Girl c. 2004 advice but really, really. Something smart and a bit more expensive does go a long way into tricking bouncers/PRs/friends from up north who like to get dressed up/yourself into thinking you’ve put some effort in.

And despite what I just said about a complementary colour with your t-shirt, I’m definitely also a fan of a bit of bright colour to add a bit of contrast. Some might even say a colour pop. I mean no-one should say that, but some might.

Needless to say I’d never be able to carry off a skirt this short, but just imagine old-faithful black opaques in there too.

The kind of dressed-up work outfit

[T-shirt; sunglasses; bag; skirt; jacket; earrings; shoes]

How I wish this Suno skirt was mine.


This feels classic poor-quality styling advice but hey. A surefire way of making a kinda grungy t-shirt look smarter would be pairing it with a slightly more luxe bottom half. Texture and fabric choice would be one way of achieving this, but why not go the whole hog and consider shape too?

I know! I think pencil skirt and t-shirt definitely has potential to look a bit wacky emo girl combining a slogan t-shirt with their bondage skirt, but  I reckon it can work.

I’m not entirely sure that I’d wear a look of such sparkle and shade spectrum for fear of total ridicule but hopefully it gets the point across; slightly fitted t-shirt and more fitted bottom half in complementary colours. Accessories that add a bit of something exciting. Nice shoes. Leather jacket. That’s the rules.

These are some thoughts anyway.

If in doubt, I’d just stick ‘Taylor Tomasi Hill skirt‘ in Google and hope for the best, because that woman does skirts better than anyone. See?

[Picture: We Have No Style]


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